Antipyretic



Patented June 15, 1926.

Wire!) STATES.

PATENT, oFncE.

WERIEEB SCHULEMANN, OI VOEWINIEL, um ILBEBI'ELD, AND FRITZ 5036K- HOI'EB, OI ELIBEBI'ELD, enmumr, LBSIGHOBB TO WINTEROP OHIIIGAL COI- PANY, 1110., OF NEW YORK, N. Y.

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Io Drawing. Application med November, 21, 1925, Berial 170. 70,874, and in Germany April 4, 1924.

The present invention relates to the manufacture and production of the hitherto unknown -ortho-acetoxyara-methoxybenzoic 5 acid having most proba ly the formula:

' coon O .OG-GHI consists in cautiously acetylating the paramethoxy-ortho-hydroxy-benzoic acid. this process'the formation of other similar :5 products (Berichte 24, 2852; Journal of the Chemical Society 107, 1494) of other melting points which do not possess the valuable therapeutic properties of our new compoundis avoided.

, more fully the following example is given:

168 parts by weight of para-methoxy-ortho-hydroxy-benzoic acid are dissolved in Y 300 parts b weight of ether (free from water) and t is solution is boiled for 1.-1 days together, with. 115 parts by weight 0% acetic acid anhydride. The ether is dis-- tilled ofi. The remaining oil soon solidifies r to a crystalline cake. It crystallizes from In order to illustrate, our new process alcohol in the shape of needles melting at from 119-121? C.

t The sodium salt can be obtained by treatmg the solution of the acid in acetone and water with sodium carbonate and precipitating the salt with ether. It is soluble in water. With ferric chloride a yellowish brown precipitate results melting at 258- This application is a continuation in of our application Serial No. 20,544, A ril 3 1925.

e ciaim: 3

1. Process for producing ortho-acetoxyara-methoxy-benzoic acid which comprises eating para-metho :ortho-hydroxy-benzoic acid with acetic t begdride. o 2. The heremdescri new ortho-acetoxypara-inethoxy-benzoic acid havingmost probably the formula:

. coon needles melting at from 119e-121"C., ing a valuable antipyretic, an average single dose being from 0.5-1 am and forming salts with alkali metals which retain the crystallizing fromalcohol in the she of valuable therapeutic properties of the free acid, substantially as described.

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WERN R SCHULEMANN. FRITZ 'SCHGNHOFER;

In testimony whereof, we ailixioup'signa- 

